Tetrahedron Letters

Efficient C-3 functionalization of 4-dimethylaminopyridine (DMAP). A straightforward access to new chiral nucleophilic catalysts

T Poisson, S Oudeyer, V Levacher

Index: Poisson, Thomas; Oudeyer, Sylvain; Levacher, Vincent Tetrahedron Letters, 2012 , vol. 53, # 26 p. 3284 - 3287

Full Text: HTML

Citation Number: 4

Abstract

Herein, the straightforward C-3 functionalization of 4-dimethylaminopyridine (DMAP) backbone is disclosed. An efficient halogen-metal exchange procedure from 3-bromo DMAP 1 is reported providing a large panel of C-3 functionalized DMAPs. In addition, a Pd- catalysed C–N cross-coupling reaction is also described furnishing new 3-amino DMAPs. These new functionalization pathways led to the resolution-free synthesis of three new ...